If I wanna learn Pudge from the pros, which people should I check out to watch replays of?
People will say Dendi but I think it's better to pay attention to good players who you play with or against.
What inevitably happens if you watch pros is you latch onto gimmicks and tricks they do, which while impressive don't demonstrate the real strength of their ability, which is usually mental (awareness, aggression, other factors), and is hard to follow in watching a replay.
When you play against or with them yourself, you get a much better grasp of what they've done that you want to replicate, and it's easier to be aware of the circumstances because you've experienced them personally. For example "I was feeling frustrated because I was getting killed trying to push bot, so I went top to farm but Pudge was there waiting for me and hooked me from the tower to the jangle. He knew it's where I'd go after getting isolated and ganked several times." These behavioral patterns are more important than looking for gimmicks like force staffing yourself to a ledge then hooking them up there. You need to experience that frustration or that understanding of the phases of the game and where you are.
Stuff like, when its good to be solo, when its good to be with the team... these are important, but should be measured based on the circumstances of the game and not watching a replay to see "okay, Dendi was solo ganking to level 8, then started team fighting" because he won't follow that game to game and you shouldn't either.
You probably don't need this detailed a rundown, but there has been an influx of new players due to mass invites so maybe others will benefit from my anecdotes..